3451-02-3

Basic information

• Product Name: 1,2,3,4-Benzenetetracarboxylic acid, tetramethyl ester
• Synonyms: benzene-1,2,3,4-tetracarboxylic acid tetramethyl ester;1,2,3,4-Benzoltetracarbonsaeure-tetramethylester;mellophanic acid tetramethyl ester;1,2,3,4-Benzenetetracarboxylic acid, tetramethyl ester;1,2,3,4-Benzenetetracarboxylic acid,tetramethyl ester;Benzol-1,2,3,4-tetracarbonsaeure-tetramethylester;Tetramethyl 1,2,3,4-benzenetetracarboxylate
• CAS NO: 3451-02-3
• Molecular Formula: C14H14O8
• Molecular Weight: 310.26
• Mol File: 3451-02-3.mol

Chemical Properties

• Melting Point: 129 °C
• Boiling Point: 341.7±37.0 °C(Predicted)
• Density: 1.287±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,2,3,4-Benzenetetracarboxylic acid, tetramethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Benzenetetracarboxylic acid, tetramethyl ester(3451-02-3)
• EPA Substance Registry System: 1,2,3,4-Benzenetetracarboxylic acid, tetramethyl ester(3451-02-3)

Safety Data

• Hazardous Substances Data: 3451-02-3(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Usage

a. Monomer in the production of thermosetting polymers
b. Crosslinking agent in the production of resins and adhesives
c. Component in the manufacture of industrial materials
d. Production of coatings, composites, and electrical insulating materials

Properties

a. High thermal stability
b. Chemical resistance
c. High performance characteristics

Importance

Crucial chemical in the production of various industrial materials

Upstream product

• 476-73-3 1,2,3,4-benzenetetracaboxylic acid 
• 186581-53-3 diazomethane 
• 16726-03-7 4-methyl-3-(3-methyl-but-2-enyl)-cyclohex-4-ene-1,2-dicarboxylic acid anhydride 
• 6467-01-2 Fuerstion 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 67-56-1 methanol 
• 5670-11-1 8-methoxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 64164-01-8 (E)-3-(piperidin-1-yl)acrylamide 
• 766-94-9 vinyl phenyl ether 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 41895-84-5 pyridazine-3,4,5,6-tetracarboxylic acid tetramethyl ester 
• 5665-24-7 α-Carboxy-β-(7-methoxy-2-naphthyl)-propionsaeure 
• 5665-25-8 2-(β-carboxyethyl)-7-methoxynaphthalene 
• 94112-99-9 tetramethyl 5-cyclohexene-1,2,3,4-tetracarboxylate 

Downstream Products

• 21895-62-5 benzene-1,2,3,4-tetracarboxylic acid-1,4-dimethyl ester 

Relevant articles and documents

Sustainable synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived carboxylic acids

Herein, we report a sustainable route for the synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived muconic acid and fumaric acid. The key Diels-Alder reaction constructed a cyclohexene framework substituted by four ester groups. The isolated yield of tetramethyl 5-cyclohexene-1,2,3,4-tetracarboxylate was up to 95.5percent without any catalyst used. And the hydrogenation reaction of the cycloadduct was catalyzed by commercial RANEY? Ni at room temperature and nearly 100percent yield of the cyclohexyl target products was obtained. This journal is

The palladium-catalyzed addition of various vinyl compounds to dimethyl acetylenedicarboxylate

The catalyst precursor (E = COOCH3) reacts with simple vinyl compounds and dimethyl acetylenedicarboxylate to give cyclic 1:2-, 2:1- and 2:2-addition products, namely substituted cyclohexadiene or benzene, cyclopentene and cyclooctadiene derivatives, which can be separated by column chromatography.Palladacyclopent-2-enes, palladacyclohepta-2,4-dienes and palladacyclohept-4-enes, which cannot be trapped, are suggested to be intermediates in the reaction.Different types of products are obtained depending on the nature of the vinyl compound: while α-methyl styrene gives only a cyclohexadiene species following 1:2-addition, vinyl ethers along with 1:2-addition undergo 2:1- and even 2:2-addtition, and cyclopentene and 1,5-cyclooctadiene derivatives are formed.In the course of the reaction with vinyl ethers, alcohols are formed, probably in a reductive elimination step from Pd-H-intermediates in which an alkoxy group occupies a β-position and also in palladium-mediated aromatization of initially formed alkoxy cyclohexadiene and bisalkoxy cyclohexene products.Yields and product ratios can be influence by changing the fixed ligand in the catalyst complex.

Reaction of (E)-β-Enamino Amides with Dimethyl Acetylenecarboxylate (DMAD): Formation of Benzene Derivatives, Enamino Esters, and 2-Pyridones

An investigation of the additions of (E)-enamino amides (1a-d) with DMAD has shown that they are influenced by the stereochemistry of the intermediates and the amine component of the enamine system.In dry acetonitrile (E)- benzyl(methyl)amino- (1b), (E)-pyrrolidin-1-ylamino-(1c), and (E)-piperidin-1-ylamino-(1d) acrylamides, following a known mechanism, yielded tetramethyl benzene-1,2,3,4-tetracarboxylate (5), the (E)-aminobutenedioates (6a-d), and the 3,4-bismethoxycarbonylpyridin-2(1H)-one (8).Dimethylamino-(1a) and morpholin-1-ylamino-(1e)-acrylamides, owing to the different nucleophilicity of the β-carbon, formed a zwitterion (11) which eliminated propiolamide to give only the (E)-aminobutenedioates (6a,e).

Cycloaddition Reactions of Azabenzenes, XVI. - Reactions of Pyridazinecarboxylates with Norbornene, Norbornadiene, and Dicyclopentadiene

Reaction of trimethyl 3,4,6-pyridazinetricarboxylate (1a) and tetramethyl 3,4,5,6-pyridazinetetracarboxylate (1b) with norbornadiene (2) yields trimethyl 1,2,4-benzenetricarboxylate (8a) and tetramethyl 1,2,3,4-benzenetetracarboxylate (8b), respectively. 1b and norbornene (3) or dicyclopentadiene (4) afford the polycyclic compounds 12 and 13.

New cyclopenta[a]naphthalene derivatives: Synthesis of 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene as a possible deoxyribonucleic acid binding agent

8-Methoxy-1-oxo-2,3-dihydro-1H-cyclopental[a]naphthalene (4) was converted to the oxalyl derivative (7) by treatment with diethyl oxalate in the presence of sodium ethoxide. Compound 7 in the form of the sodium salt was alkylated with ethyl bromoacetate in DMF to 2-(carbethoxymethyl)-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopenta[a]naphthalene (8). Treatment of 8 with methanolic ammonia yielded the corresponding amide (9). Dealkylation of 8 with 48% HBr and subsequent esterification gave compound 10. Ammonolysis of 10 led to the amide 11, which after reduction and subsequent dehydration of the reduced product afforded the desired compound, 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene (2). Compound 2 was found to be mildly growth inhibitory to L1210 and CCRF-CEM leukemic cells in culture. From thermal transition temperature studies, compound 2 was found to bind to calf thymus DNA and the poly(deoxyribonucleotides), e.g., poly(dG)-poly(dC), poly(dG-dC), poly(dA)-poly(dT), and poly (dA-dT).